2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine → (3S,5S)-3-methyl-5-{2-methylsulfany-l-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-ylamino}-piperidine-1-carboxylic acid benzyl ester

Participants

Reaction Steps

A degassed toluene (15 ml) solution of 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (1.0 g, 3.0 mmol), 1,1,1,2,2,2-hexamethyldistannane (1.0 g, 3.1 mmol), and tetrakis(triphenylphosphine)palladium(0) (176 mg, 0.15 mmol) was treated in a similar manner as Example 76, step 3. To this was added (3S,5S)-benzyl 3-(5-bromo-2-(methylthio)pyrimidin-4-ylamino)-5-methylpiperidine-1-carboxylate (1.37 g, 3.0 mmol) and another 176 mg of palladium catalyst and following Example 76, step 3. (3S,5S)-3-methyl-5-{2-methylsulfany-l-5-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyrimidin-4-ylamino}-piperidine-1-carboxylic acid benzyl ester (660 mg, 35%) could be isolated as an oil and taken to the next step. (0227-160)

Provenance & Evidence